One-pot multistep synthesis of 1-fluoroalkylisoquinolines and fused fluoroalkylpyridines from N-fluoroalkyl-1,2,3-triazoles
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F24%3A00587257" target="_blank" >RIV/61388963:_____/24:00587257 - isvavai.cz</a>
Alternative codes found
RIV/60461373:22310/24:43929270
Result on the web
<a href="https://doi.org/10.1039/D4QO00713A" target="_blank" >https://doi.org/10.1039/D4QO00713A</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1039/D4QO00713A" target="_blank" >10.1039/D4QO00713A</a>
Alternative languages
Result language
angličtina
Original language name
One-pot multistep synthesis of 1-fluoroalkylisoquinolines and fused fluoroalkylpyridines from N-fluoroalkyl-1,2,3-triazoles
Original language description
An efficient one-pot microwave-assisted potassium fluoride-mediated synthesis of 1-fluoroalkyl-3-fluoroisoquinolines and fused fluoroalkylpyridines from N-fluoroalkylated 1,2,3-triazoles was developed. The reaction has a wide scope and allows the preparation of structurally diverse 3-fluoroisoquinolines with a fluoroalkyl group in position 1, a substituent in position 4 and a substituent on the fused benzene (or heteroaromatic) ring. N-Fluoroalkylated ketenimines, which undergo stereoselective formal 1,3-fluorine shift to difluoroazadienes, were identified as intermediates in the reaction sequence. The presence of fluorine in position 3 and a halogen in position 4 of the resulting isoquinolines allowed for further modification by nucleophilic aromatic substitution and cross-coupling reactions, respectively. The developed methodologies were utilized for the synthesis of derivatives of drug candidates.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
<a href="/en/project/GA23-04659S" target="_blank" >GA23-04659S: Utilization of organic fluorinated azides for the synthesis of unusual nitrogen heterocycles</a><br>
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2024
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Organic Chemistry Frontiers
ISSN
2052-4129
e-ISSN
2052-4129
Volume of the periodical
11
Issue of the periodical within the volume
16
Country of publishing house
GB - UNITED KINGDOM
Number of pages
7
Pages from-to
4442-4448
UT code for WoS article
001253287100001
EID of the result in the Scopus database
2-s2.0-85197864759